Depending upon how hurricane season is looking of course, I am looking to head to the Caribbean sometime in November and am trying to get an idea of where a good place to start would be to connect/network with sailboats and join as crew- unpaid, paid, paying... Ideally I'd like to cruise the Caribbean for a couple/few months, possibly even jump ship and try to work a bit, then head on to South America- Venezuela as the entry point. Sound feasible, reasonable, etc.? I greatly appreciate any and all input! Thanks for taking the time to read, and answer!

St. Martin (both sides) and Antigua are, in my opinion, the best places to look for berths on boats.
In St. Martin there are a couple of crew-hangout bars - the Palapa Marina bar at the forefront and then places like Jimbo's [the latter is a personal preference, since I like Blues and Rock music].
On Antigua the chances of finding a berth are best at Mad Mongoose in Falmouth harbour. Excepting teetotalers, every Captain will, at some point, gravitate to that bar. During the day and before the bar/restaurant itself opens, just hang out at the free WiFi stations outside and talk to the boaties coming by. Antigua also has a couple of well-placed bulletin boards which are read by crews so you chances are maximized. Both locations are good for both free and paid crew, but in order to qualify for the latter you would need to have a STCW.

Either option sounds like it will work nicely, St. Martin seems to often come to mind when I'm thinking of the Caribbean.

Being a seasoned sailor, do you think it worth my while to do the STCW in the States whilst I am still here or would there be an opportunity to do it in the Caribbean, maybe even a little less expensively? Also, given the fact that I am a (fit and able-bodied) woman in my 40th year, am I dreaming thinking that someone would actually want to take me on as paid crew? Not new to sailing but new to the cruising life... thanks again for the info, as well as the patience in answering my questions!!

MarkCK - STCW is a certification, it stands for "Standards of Training, Certification and Watchkeeping" and there are various levels, but the basics are now required for most paid positions and have therefore become an international prerequisite.
intoliquid - I would do the courses at home. I have seem training offerred in Antigua but at a guess the scheduling and pricing won't be as good as at home. From my sessions (at the bar) with crews and officers of megayachts and just plain 'ole vanilla big yachts, they are often looking for crew to fill in the non-specialist positions on their boats. These positions pay (not much, but they do pay) but are limited to those with qualifications.
Your chances of getting a position which doesn't pay but offers bunk & board are much better but those boats will be normal sized yachts. Often they will take on crew for long passages or to cover for a guest/crewmember who didn't show up. In those cases you would have a lot better chances if you could share watches or cook or perform some specialized task.
The www.crewfinders.net works for unpaid positions, but crew finders as mentioned above will point you at the commercial side.
The STCW is only worth doing if your goal is to get your entry ticket to crewing on larger yachts.

I know this is a question that doesnt have an good easy answer, but if you were certified how much could you expect to make in an entry level position? I am just curious.

Life is not good in the paid crew world just now. There are highly qualified crew working just for their keep with zero salary.

However if you have a sailing partner WHO CAN COOK then there are some temporary posts around for couples with the charter companies who want skipper/cook combinations to take charterers out when they do not have sufficient experience to look after themselves.

The Moorings is one such company who employ skipper/cook combinations and who pay them reliably.

Ah, in light of all of this new information I reckon I shall stay with my original idea of heading down, not actually earning any money until I hit land for a spell. Everything for good reason! Thank you all for all of the contributions!

Another good place to hook up with boats looking for crew is St. Lucia after the ARC boats arrive. You won't find any paying positions but could get a ride on a shared expense basis.
Also when the European boats return home in May you can get a ride across and you would only have to pay your flights to and from the boat.

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